diff --git a/Oqtane.Client/Modules/Admin/Site/Index.razor b/Oqtane.Client/Modules/Admin/Site/Index.razor
index 115f29a0..7e1385ff 100644
--- a/Oqtane.Client/Modules/Admin/Site/Index.razor
+++ b/Oqtane.Client/Modules/Admin/Site/Index.razor
@@ -224,11 +224,14 @@
                         </div>
                     </div>
                     <div class="row mb-1 align-items-center">
-                        <Label Class="col-sm-3" For="smtpssl" HelpText="Specify if SSL is required for your SMTP server" ResourceKey="SmtpSSL">SSL Required: </Label>
+                        <Label Class="col-sm-3" For="smtpssl" HelpText="Specify the type of SSL connection for your SMTP server" ResourceKey="SmtpSSL">SSL Options: </Label>
                         <div class="col-sm-9">
-                            <select id="smtpssl" class="form-select" @bind="@_smtpssl" >
-                                <option value="True">@SharedLocalizer["Yes"]</option>
-                                <option value="False">@SharedLocalizer["No"]</option>
+                            <select id="smtpssl" class="form-select" @bind="@_smtpssl">
+                                <option value="None">@Localizer["None"]</option>
+                                <option value="Auto">@Localizer["Auto"]</option>
+                                <option value="StartTls">@Localizer["StartTls"]</option>
+                                <option value="SslOnConnect">@Localizer["SslOnConnect"]</option>
+                                <option value="StartTlsWhenAvailable">@Localizer["StartTlsWhenAvailable"]</option>
                             </select>
                         </div>
                     </div>
@@ -504,7 +507,7 @@
     private string _smtpauthentication = "Basic";
     private string _smtphost = string.Empty;
     private string _smtpport = string.Empty;
-    private string _smtpssl = "True";
+    private string _smtpssl = "Auto";
     private string _smtpusername = string.Empty;
     private string _smtppassword = string.Empty;
     private string _smtppasswordtype = "password";
@@ -613,7 +616,9 @@
                 {
                     _smtphost = SettingService.GetSetting(settings, "SMTPHost", string.Empty);
                     _smtpport = SettingService.GetSetting(settings, "SMTPPort", string.Empty);
-                    _smtpssl = SettingService.GetSetting(settings, "SMTPSSL", "False");
+                    _smtpssl = SettingService.GetSetting(settings, "SMTPSSL", "Auto");
+                    if (_smtpssl == "True") _smtpssl = "SslOnConnect";
+                    if (_smtpssl == "False") _smtpssl = "StartTlsWhenAvailable";
                     _smtpauthentication = SettingService.GetSetting(settings, "SMTPAuthentication", "Basic");
                     _smtpusername = SettingService.GetSetting(settings, "SMTPUsername", string.Empty);
                     _smtppassword = SettingService.GetSetting(settings, "SMTPPassword", string.Empty);
diff --git a/Oqtane.Client/Resources/Modules/Admin/Site/Index.resx b/Oqtane.Client/Resources/Modules/Admin/Site/Index.resx
index 97e4e8f3..5379db80 100644
--- a/Oqtane.Client/Resources/Modules/Admin/Site/Index.resx
+++ b/Oqtane.Client/Resources/Modules/Admin/Site/Index.resx
@@ -193,7 +193,7 @@
     <value>Enter the port number for the SMTP server. Please note this field is required if you provide a host name.</value>
   </data>
   <data name="SmtpSSL.HelpText" xml:space="preserve">
-    <value>Specify if SSL is required for your SMTP server</value>
+    <value>Specify the type of SSL connection for your SMTP server</value>
   </data>
   <data name="SmtpUsername.HelpText" xml:space="preserve">
     <value>Enter the username for your SMTP account</value>
@@ -241,7 +241,7 @@
     <value>Port: </value>
   </data>
   <data name="SmtpSSL.Text" xml:space="preserve">
-    <value>SSL Required: </value>
+    <value>SSL Options:</value>
   </data>
   <data name="SmtpUsername.Text" xml:space="preserve">
     <value>Username: </value>
@@ -489,4 +489,19 @@
   <data name="SmtpAuthority.HelpText" xml:space="preserve">
     <value>The Authority Url for the SMTP provider</value>
   </data>
+  <data name="None" xml:space="preserve">
+    <value>None</value>
+  </data>
+  <data name="Auto" xml:space="preserve">
+    <value>Automatic</value>
+  </data>
+  <data name="StartTls" xml:space="preserve">
+    <value>Upgrade To TLS</value>
+  </data>
+  <data name="SslOnConnect" xml:space="preserve">
+    <value>Require SSL/TLS</value>
+  </data>
+  <data name="StartTlsWhenAvailable" xml:space="preserve">
+    <value>Use TLS When Available</value>
+  </data>
 </root>
\ No newline at end of file
diff --git a/Oqtane.Server/Infrastructure/Jobs/NotificationJob.cs b/Oqtane.Server/Infrastructure/Jobs/NotificationJob.cs
index 6b755e89..65b53cc0 100644
--- a/Oqtane.Server/Infrastructure/Jobs/NotificationJob.cs
+++ b/Oqtane.Server/Infrastructure/Jobs/NotificationJob.cs
@@ -81,9 +81,31 @@ namespace Oqtane.Infrastructure
                         // construct SMTP Client
                         using var client = new SmtpClient();
 
+                        var secureSocketOptions = SecureSocketOptions.Auto;
+                        switch (settingRepository.GetSettingValue(settings, "SMTPSSL", "Auto"))
+                        {
+                            case "None":
+                                secureSocketOptions = SecureSocketOptions.None;
+                                break;
+                            case "Auto":
+                                secureSocketOptions = SecureSocketOptions.Auto;
+                                break;
+                            case "StartTls":
+                                secureSocketOptions = SecureSocketOptions.StartTls;
+                                break;
+                            case "SslOnConnect":
+                            case "True": // legacy setting value
+                                secureSocketOptions = SecureSocketOptions.SslOnConnect;
+                                break;
+                            case "StartTlsWhenAvailable":
+                            case "False": // legacy setting value
+                                secureSocketOptions = SecureSocketOptions.StartTlsWhenAvailable;
+                                break;
+                        }
+
                         await client.ConnectAsync(settingRepository.GetSettingValue(settings, "SMTPHost", ""), 
-                                    int.Parse(settingRepository.GetSettingValue(settings, "SMTPPort", "")),
-                                    bool.Parse(settingRepository.GetSettingValue(settings, "SMTPSSL", "False")) ? SecureSocketOptions.StartTls : SecureSocketOptions.None);
+                                int.Parse(settingRepository.GetSettingValue(settings, "SMTPPort", "")),
+                                secureSocketOptions);
 
                         if (settingRepository.GetSettingValue(settings, "SMTPAuthentication", "Basic") == "Basic")
                         {